It demands the sort of agility more often seen among a group of contortionists, the full-back inclined also to stare at his feet given how lowly his side were back then. Wilson made his United debut in 2000 in a spell which would span six years, most of which were notable only for a dearth of success as the Tannadice side toiled around the foot of the Scottish top flight.
It was a period of the club's history when players would also rub shoulders with their counterparts at Aberdeen quite regularly, mainly as the two teams would try to use one another as a buffer against the threat of relegation. Now 29, Wilson will today reprise that role with the merciful twist that his club make the trip to Pittodrie with intentions of beating their hosts to a spot in the qualifying rounds of the Europa League.
Aberdeen lead by five points in the SPFL Premiership table, looking down on United from on high. Or second place as it known. That has often seemed fitting this season given that the Pittodrie side are walking tall; a win in the League Cup final achieved alongside an enduring effort to return to Europe.
United are a little further behind - they are also fully four points behind Motherwell as well - but have found incentive to keep up the chase after enjoying a relatively successful campaign of their own. The emergence of bright talents such as Ryan Gauld, John Souttar and Ryan Dow have been among the highlights for Wilson.
"This is probably the best shape I can remember both Dundee United and Aberdeen going into one of these matches," added Wilson, whose side are without on-loan Newcastle United defender Curtis Good for the trip to the north east. "When I first started playing in them we were both at the bottom end of the table. At United we weren't having a great time and Aberdeen were worse than us . . .
"We had a few relegation battles. They were important games but you'd much rather be going into matches at the top end of the table. It has turned around now and it's great to see the clubs up there.
"It sounds rubbish saying it, but we should be competing for second place. Everyone would love it to get back to the 1980s, when United and Aberdeen were competing for titles and in the latter stages of Europe. But that's not going to happen."
It was a moment of realism which was interrupted by the acknowledgement that Stewart Milne, Aberdeen's chairman, has already tried to incite other teams to challenge Celtic in the league. That is a reach, even for the Pittodrie side. They are 26 points behind champions Celtic.
That gap will appear even wider for Wilson. The defender left Tayside to sign for Celtic eight years ago and knows better than most the size and strength of the Glasgow club. "Is it unrealistic to expect ourselves or Aberdeen to challenge Celtic? If I'm being totally honest, then yes," said the 29-year-old.
"That is years away at the moment. Celtic make mistakes much more rarely than the likes of ourselves, Aberdeen or Motherwell. That's why they are able to pull away from the rest of us and win titles the way they are. They have been able to get a level of consistency that we have to aim for now."
Despite the sense of success which has shone over Pittodrie of late, there are still those eager to find ways to better themselves. Among them is Joe Shaughnessy - a defender who would start the season as a familiar face in the starting XI but who has slipped from view of late. That has been due to the arrival of Shay Logan on loan from Brentford, at least in part, with the Englishman consolidating a place in the first team since alighting in the north east.
It has left Shaughnessy with an obscured view, but he has still seen enough that the defender is confident that he will be able to improve on aspects of his game. He is expected to be given his opportunity to put into practice what he has learned this afternoon, with Logan likely to fill in at left-back as a result of Andrew Considine's suspension.
"I think [Logan] has done really well since he came in," said Shaughnessy, whose side could also restore Peter Pawlett to the squad, while Jonny Hayes is also sidelined with a shoulder injury. "He is a different player to myself; he is quite attacking and sharp and has been playing really well. There is no reason for him to be out of the team.
"He is more of an attacking full-back than myself. I watch him and try to improve that side of my game as well. He has been quite impressive. I think it will be really exciting. It will be a tough game, but everyone is looking forward to it. It has been quite an exciting couple of weeks."